Valparaiso & Viña del Mar: Port Walks, Street Art & Casablanca Wine

Summary

Street art, sea lions, funicular rides and Chilean wine in one day

You’ll wander Valparaiso’s painted hills, ride an old funicular with locals, spot sea lions by the port, and sample Casablanca wines surrounded by vines. Taste street food or pause at a viewpoint—the day moves at a local rhythm. By sunset you’ll carry home more than photos: maybe a new favorite flavor or a memory that lingers unexpectedly.

What’s the experience like?

I didn’t expect the first thing I’d see in Viña del Mar to be a Moai statue from Easter Island, just standing there outside the Fonck Museum. Our guide, Camila, grinned at my surprise and told us how it ended up here in 1951. She had this way of mixing history with little jokes—like when she tried to teach us to say “Rapa Nui” properly (I definitely failed). The air smelled faintly salty even so far from the beach, and kids were already running circles around the flower clock as we passed by.

Valparaiso is louder than I thought—colors everywhere, dogs barking from rooftops, that echo of music somewhere up the hill. Walking those steep streets feels like wandering inside a painting that’s half graffiti and half old European architecture. We squeezed into one of those wooden funiculars—the Ascensor El Peral creaked but made it up—and at the top, Camila pointed out the bay stretching forever. There was this moment on Paseo Gervasoni where I just stood quiet for a second; you could smell frying fish drifting up from the port below and hear street artists laughing behind us. I still think about that view sometimes.

Lunch was our own choice (I went for empanadas—probably too many), then we drove out to Casablanca Valley. The vineyards looked almost unreal against all that dry land. The wine tasting wasn’t rushed; we tried two kinds while someone explained how the sea breeze changes everything about the grapes here. I’m not really a wine person but even I could taste something different—fresher maybe? It felt good to sit for a bit after so much walking. On the way back to Santiago (or if you’re heading to your cruise ship), everyone was quieter than before—maybe tired or just letting it all sink in.

Step-by-step itinerary

Day 1 — Valparaiso and Casablanca wine tasting

• Pick up at accommodation around 8 AM
• Visit Corporate Museum of Archaeology and History
• See Moai statue from Easter Island
• View Viña del Mar coastline and Cerro Castillo
• Visit old German family castle
• Walk through Viña del Mar flower garden and clock
• Panoramic city view of Viña del Mar
• Pass by first casino in Chile
• Visit fish market and sea lions spot
• See British donation monument from 1910
• Explore Plaza Sotomayor and Navy headquarters
• View Monument to the heroes of the Pacific War
• Panoramic view of Valparaiso city
• Take Ascensor El Peral elevator
• Visit Baburizza Palace art museum
• Walk famous walkway with sea views
• See Italian community stairs and taste alfajores
• Walk through Valparaiso wall art alleyways
• Walking tour of Cerro Concepcion hill
• Visit Paseo Gervasoni walkway and ascensor
• Walking tour of UNESCO World Heritage highlights
• View wall art on Valparaiso stairs
• Walk alley to Reina Victoria's Ascensor
• Walk famous east side Valparaiso walkway
• Wine tasting at Casablanca Valley winery
• Drop off at Cruise ship terminal in San Antonio Port

Top questions

Is hotel pickup included for this Valparaiso & Viña del Mar tour?

Yes, hotel pickup and drop-off are included from Santiago accommodations.

Does this day trip include wine tasting in Casablanca Valley?

Yes, there is a wine tasting stop at a vineyard in Casablanca Valley on the return journey.

Can I bring luggage if I need drop-off at Valparaiso port?

You can bring 1 large and 1 small luggage per person if you request drop-off at Valparaiso port; extra luggage may require an additional fee.

If I get dropped off at Valparaiso port for my cruise, do I miss anything?

If you choose drop-off at Valparaiso port instead of returning to Santiago, you will miss the winery stop in Casablanca Valley.

Are entrance fees or funicular rides included?

The tour includes one funicular ride in Valparaiso as part of your experience.

What time does this day trip usually start and end?

Pickup is around 8 AM; drop-off is between 6:00 PM and 7:00 PM depending on traffic and itinerary pace.

Is lunch included during this tour?

No, lunch is not included—you can choose where to eat during free time in Valparaiso or Viña del Mar.

Is this tour suitable for all fitness levels?

The tour is suitable for all physical fitness levels but involves some walking on hilly streets.

What’s included

Your day includes pickup from your Santiago hotel, one classic funicular ride through Valparaiso’s hills with your guide leading the way, entry to key sites along both cities’ routes, wine tasting at a Casablanca Valley vineyard (unless you opt for cruise ship drop-off), plus return transport or direct transfer to your ship—all arranged so you can just enjoy each moment as it comes.